Compound ID | 1865

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Ertapenem

Class: Beta-lactam (carbapenem)

Spectrum of activity: Gram-negative
Details of activity: Binds to bacterial penicillin-binding proteins (PBP) and interferes with bacterial cell wall integrity and synthesis. Carbapenems bind to all PBPs, with PBP2 and PBP4 as the highest-affinity targets. Ertapenem is mainly active against Enterobacteriaceae and has a longer half life than othe carbapenems
Description: Semisynthetic, derived from thienamycin. Longer half live
Institute where first reported: MSD/Merck
Year first mentioned: 1992
Highest developmental phase: Approved by FDA in 2001
Development status: Approved, off-patent
Chemical structure(s):
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Molecular weight: 475.52
Iso. SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)NC4=CC=CC(=C4)C(=O)O)C(=O)O)[C@@H](C)O
InChI Key: JUZNIMUFDBIJCM-ANEDZVCMSA-N
Can. SMILES: C[C@@H]1[C@@H]2[C@@H]([C@@H](C)O)C(=O)N2C(=C1S[C@H]3C[C@@H](C(=O)NC4=CC(=CC=C4)C(=O)O)NC3)C(=O)O
InChI: InChI=1S/C22H25N3O7S/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32)/t9-,10-,13+,14+,15-,16-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/150610
Guide to Pharmacology: ertapenem
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/17488146/
  • https://pubmed.ncbi.nlm.nih.gov/27101841/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6535521/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4867097/

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